25826-75-9

Upstream product

• 27729-95-9 trans-4-methoxychalcone epoxide 
• 24845-40-7 2-(4-methoxyphenyl)acetophenone 
• 109-94-4 formic acid ethyl ester 
• 6969-02-4 [3-(4-methoxyphenyl)oxiran-2-yl]phenylmethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 

Downstream Products

• 1430342-25-8 2-(4-methoxyphenyl)-3-hydroxy-1-phenylpropan-1-one 
• 86387-70-4 2-(p-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 57479-32-0 3-(4-methoxyphenyl)quinoline 
• 113380-90-8 4-(4-methoxyphenyl)-1,5-diphenyl-1H-pyrazole 

Relevant academic research and scientific papers

Metal-free, one-pot, sequential protocol for transforming ,-epoxy ketones to -hydroxy ketones and -methylene ketones

A new sequential, one-pot protocol for transforming 1,3-disubstituted 2,3-epoxy ketones to β;-hydroxy ketones and α-methylene ketones has been developed. Reaction of epoxy ketones with boron trifluoride etherate (BF3·OEt2) generates the cationic intermediates by regioselective epoxide ring opening and an acyl shift. Then, a treatment of these cations with 2-aryl-1,3-dimethylbenzimidazolines (DMBIH) results in formation of 1,2-disubstituted 3-hydroxy ketones. DMBIH serves as a hydride donor in the second step of this process. Finally, the β;-hydroxy ketones can be converted to 1,2-disubstituted 2-methylene ketones by treatment with methanesulfonic acid or a combination of methanesulfonyl chloride and triethylamine. Importantly, the sequential steps involved in formation of the α-methylene ketone products can be carried out in one pot.

Practical approach for preparation of unsymmetric benzils from β-ketoaldehydes

An efficient and practical method for the synthesis of unsymmetric benzils from readily available β-ketoaldehydes has been developed. Various unsymmetric 1,2-diaryldiketones bearing functional groups have been obtained in good to excellent yields under mild reaction conditions. A plausible mechanism was proposed, and α,α-dichloroketone was considered as the key intermediate. The generation of α,α-dichloroketones from β-ketoaldehydes may undergo the following steps: (1) oxidation by sodium hypochlorite, (2) decarboxylation, and (3) chlorination by Cl2 generated from sodium hypochlorite.

Selective Cβ-O Bond Cleavage of Chalcone Epoxides Induced by Pyrylium Salt Sensitized Photoreactions and Dark Reactions with Cerium(IV) Salts

The Cβ-O bonds of chalcone epoxides (1a, 1b) were selectively cleaved by pyrylium salt sensitized photoreactions, affording β-ketoaldehydes (2a, 2b) in CH2Cl2 and MeOH-adducts (3a, 3b) in MeOH.Similarly, cerium(IV) salts catalyzed the MeOH-adduct formations of 1a and 1b in the dark.On the other hand, nitrate ester (4b) was obtained on treatment of 1b with a cerium(IV) salt in MeCN.